4-(2-Pyrimidinyl)-1-piperazinebutanamine → 3-[4-[4-(2-Pyrimidinyl)-1-piperazinyl]butyl]-8,8-dimethyl-3-azabicyclo[3.2.1]octane-2,4-dione

HRID 4920

Reaction equation

HRID 4920 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][N:9]([C:12]2[N:17]=[CH:16][CH:15]=[CH:14][N:13]=2)[CH2:8][CH2:7]1.[CH3:18][C:19]1([CH3:29])[CH:24]2[CH2:25][CH2:26][CH:20]1[C:21](=O)[O:22][C:23]2=[O:27]>>[N:17]1[CH:16]=[CH:15][CH:14]=[N:13][C:12]=1[N:9]1[CH2:8][CH2:7][N:6]([CH2:5][CH2:4][CH2:3][CH2:2][N:1]2[C:23](=[O:27])[CH:24]3[C:19]([CH3:18])([CH3:29])[CH:20]([CH2:26][CH2:25]3)[C:21]2=[O:22])[CH2:11][CH2:10]1

Participants

3

Reactant 2

HCID 128407054-(2-Pyrimidinyl)-1-piperazinebutanamineHCID 197972038,8-Dimethyl-3-oxabicyclo(3.2.1)octane-2,4-dione

Product 1

HCID 140971643-[4-[4-(2-Pyrimidinyl)-1-piperazinyl]butyl]-8,8-dimethyl-3-azabicyclo[3.2.1]octane-2,4-dioneYield 32%

Procedure

Following substantially the procedure of Example 1, 0.54 g (2.34 mmol) of 1-(4-aminobutyl)-4-(2-pyrimidinyl) piperazine was reacted with 0.36 g (2.14 mmol) of 8,8-dimethyl-3-oxabicyclo[3.2.1]octan-2,4-dione. The product was chromatographed on silica gel, eluting with dichloromethane/methanol (96:4), to give 0.25 g (32% yield) of the title compound.

Workup

  1. customThe product was chromatographed on silica gel
  2. washeluting with dichloromethane/methanol (96:4)

Sources & evidence

ORD record
ord-1790a349503649588a9f0cb35a4defe4
Source dataset
uspto-grants-1993_09
Patent number
US05242911

Linked notes

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